Nitroethane → HCID 69640425, compound

HRID 1370186Notes

Reaction equation

HRID 1370186 reaction equation
[CH2:1]1[C:5]2=[C:6]([CH:13]=O)[C:7]3[CH:8]=[CH:9][CH:10]=[N:11][C:12]=3[N:4]2[CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+].[N+:20]([CH2:23][CH3:24])([O-:22])=[O:21]>>[N+:20]([C:23]([CH3:24])=[CH:13][C:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[N:11][C:12]=2[N:4]2[CH2:3][CH2:2][CH2:1][C:5]=12)([O-:22])=[O:21]

Participants

4

Reactant 3

HCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 18510482HCID 18510482, compound

Product 1

HCID 69640425HCID 69640425, compoundYield 80%

Procedure

A stirred solution of 2,3-dihydro-1H-3a,4-diaza-cyclopenta[a]indene-8-carbaldehyde (2.3 g) and ammonium acetate (1.05 g) in nitroethane was heated to 100° C. for 2.5 h, cooled to room temperature, and evaporated under reduced pressure. The residue was partitioned between water and ethyl acetate, the phases separated, the aqueous phase re-extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane 2:1 to 4:1) to afford 8-(2-nitropropenyl)-2,3-dihydro-1H-3a,4-diaza-cyclopenta[a]indene as a yellow solid (2.4 g, 80%); MS (EI) 244 (M+H)+, 224, 195, 171; 1H NMR (δ, CDCl3) 8.31 (dd, 1H, J=1,5 Hz), 8.29 (s, 1H), 7.92 (dd, 1H, J=1,8 Hz), 7.16 (dd,1H, J=5,8 Hz), 4.34 (t,2H, J=6 Hz), 3.18 (t,2H, J=8 Hz), 2.72 (dt,2H, J=6,8 Hz), 2.45 (s,3H) ppm.

Workup

  1. customevaporated under reduced pressure
  2. customThe residue was partitioned between water and ethyl acetate
  3. customthe phases separated
  4. extractionthe aqueous phase re-extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate/hexane 2:1 to 4:1)

Sources & evidence

ORD record
ord-e2cd4321192d48ba81de9ecbe70f87ec
Source dataset
uspto-grants-2003_06
Patent number
US06583134B2

Reaction notes

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